Metal-based inhibitors of protein tyrosine phosphatases

Anti-Cancer Agents in Medicinal Chemistry

Volumn 11, Issue 1, 2011, Pages 164-171

  Lu, Liping ^a   Zhu, Miaoli ^a  

^a SHANXI UNIVERSITY   (China)

Author keywords

Copper complexes; Gold complexes; Inhibitor; Metal complexes; Metal ions; Phosphorylation; Protein tyrosine phosphatases; Selectivity; Vanadium complexes; Zinc complexes

Indexed keywords

COPPER COMPLEX; GOLD COMPLEX; METAL COMPLEX; METAL ION; PROTEIN TYROSINE PHOSPHATASE; PROTEIN TYROSINE PHOSPHATASE INHIBITOR; VANADIUM DERIVATIVE; ZINC COMPLEX;

AUTOIMMUNE DISEASE; DIABETES MELLITUS; ENZYME ACTIVITY; ENZYME INHIBITION; NEUROLOGIC DISEASE; PROTEIN PHOSPHORYLATION; REVIEW; SIGNAL TRANSDUCTION;

EID: 79952995493     PISSN: 18715206     EISSN: None     Source Type: Journal    
DOI: 10.2174/187152011794941271     Document Type: Review

References (86)

1. Rosenberg, B.; VanCamp, L.; Trosko, J. E.; Mansour, V. H. Platinum compounds - A new class of potent antitumour agents. Nature, 1969, 222, 385-386.
2. Ronconi, L.; Sadler, P. J. Using coordination chemistry to design new medicines. Coord. Chem. Rev., 2007, 251, 1633-1648.
3. Bruijnincx, P. C. A; Sadler, P. J. New trends for metal complexes with anticancer activity. Cur. Opin. Chem. Biol., 2008, 12, 197-206.
4. Van Rijt, S. H.; Sadler, P. J. Current applications and future potential for bioinorganic chemistry in the development of anticancer drugs. Drug Discov. Today, 2009, 14, 1089-1097.
5. Crans, D. C.; Smee, J. J.; Gaidamauskas, E.; Yang, L. The chemistry and biochemistry of vanadium and the biological activities exerted by vanadium compounds. Chem. Rev., 2004, 104, 849-902.
6. Frezza, M.; Hindo, S.; Chen, D.; Davenport, A.; Schmitt, S.; Tomco, D.; Dou, Q.P. Novel metals and metal complexes as platforms for cancer therapy. Curr. Pharm. Des. 2010, 16, 1813-1825.
7. Khan, G.; Merajver, S. Copper chelation in cancer therapy using tetrathiomolybdate: an evolving paradigm. Expert Opin. Investig. Drugs, 2009, 18, 541-548.
8. Suna, R. W.-Y.; Che, C.-M. The anti-cancer properties of gold(III) compounds with dianionic porphyrin and tetradentate ligands. Coord. Chem. Rev., 2009, 253, 1682-1691.
9. Navarro, M. Gold complexes as potential anti-parasitic agents. Coord. Chem. Rev., 2009, 253, 1619-1626.
10. Kostova, I. Ruthenium complexes as anticancer agents. Curr. Med. Chem., 2006, 13, 1085-1107.
11. Wang, X.; Guo, Z. Towards the rational design of platinum(II) and gold(III) complexes as antitumour agents. Dalton Trans., 2008, 1521-1532.
12. Ge, R.; Sun, H. Bioinorganic chemistry of bismuth and antimony: target sites of metallodrugs. Acc. Chem. Res., 2007, 40, 267-274.
13. Bishayee, A.; Waghray, A.; Patel, M. A.; Chatterjee, M. Vanadium in the detection, prevention and treatment of cancer: the in vivo evidence. Cancer Lett., 2010, 294, 1-12.
14. Hönscheid, A.; Rink, L.; Haase, H. T-lymphocytes: a target for stimulatory and inhibitory effects of zinc ions. Endocr. Metab. Immune Disord Drug Targets, 2009, 9, 132-44.
15. Hirano, T.; Murakami, M.; Fukada, T.; Nishida, K.; Yamasaki, S.; Suzuki, T. Roles of zinc and zinc signaling in immunity: zinc as an intracellular signaling molecule. Adv. Immunol., 2008, 97,149-76.
16. Rademaker-Lakhai, J. M.; van den Bongard, D.; Pluim, D.; Beijnen, J. H.; Schellens, J. H. M. A phase I and pharmacological study with imidazolium-trans-DMSO-imidazole-tetrachlororuthenate, a novel ruthenium anticancer agent. Clin. Cancer Res., 2004, 10, 3717-3727.
17. Hartinger, C. G.; Jakupec, M. A.; Zorbas-Seifried, S.; Groessl, M.; Egger, A.; Berge, W.; Zorbas, H.; Dyson, P. J.; Keppler, B. K. KP1019, A new redox-active anticancer agent - preclinical development and results of a clinical phase I study in tumor patients. Chem. Biodivers., 2008, 5, 2140-2155.
18. Wang, T.; Guo, Z. Copper in medicine: homeostasis, chelation therapy and antitumor drug. Des. Curr. Med. Chem., 2006, 13, 525-537.
19. Marzano, C.; Pellei, M.; Tisato, F.; Santini, C. Copper complexes as anticancer agents. Anti-Cancer Agents Med. Chem., 2009, 9, 185-211.
20. Meggers, E. Targeting proteins with metal complexes. Chem. Commun., 2009, 7, 1001-1010.
21. Griffith, D.; Parker, J. P.; Marmion, C. J. Enzyme inhibition as a key target for the development of novel metal-based anti-cancer therapeutics. Anti-Cancer Agents Med. Chem., 2010, 10, 354-370.
22. Cvek, B.; Milacic, V.; Taraba, J.; Dou, Q. P. Ni(II), Cu(II), and Zn(II) diethyldithiocarbamate complexes show various activities against the proteasome in breast cancer cells. J. Med. Chem., 2008, 51, 6256-6258.
23. Meggers, E.; Atilla-Gokcumen, G.; Bregman, H.; Jasna Maksimoska, E.; Mulcahy, S. P.; Pagano, N.; Williams, D. S. Exploring chemical space with organometallics: ruthenium complexes as protein kinase inhibitors. Synlett, 2007, 1177-1189.
24. Andersen, J. N.; Jansen, P. G.; Echwald, S. M.; Mortensen, O. H.; Fukada, T.; Vecchio, R. D.; Tonks, N. K.; Møller, N. P. H. A genomic perspective on protein tyrosine phosphatases: gene structure, pseudogenes, and genetic disease linkage. FASEB J., 2004, 18, 8-30.
25. Blaskovich, M. A. T. Drug discovery and protein tyrosine phosphatases. Curr. Med. Chem., 2009, 16, 2095-2176.
26. Stuible, M.; Doody, K. M.; Tremblay, M. L. PTP1B and TC-PTP: regulators of transformation and tumorigenesis. Cancer Metastasis Rev., 2008, 27, 215-230.
27. Heinonen, K. M.; Nestel, F. P.; Newell, E. W.; Charette, G.; Seemayer, T. A.; Tremblay, M. L.; Lapp, W. S. T-cell protein tyrosine phosphatase deletion results in progressive systemic inflammatory disease. Blood, 2004, 103, 3457-3464.
28. Pao, L. I.; Badour, K.; Siminovitch, K. A.; Neel, B. G. Nonreceptor protein-tyrosine phosphatases in immune cell signaling. Annu. Rev. Immunol., 2007, 25, 473-523.
29. Vang, T.; Miletic, A.V.; Arimura, Y.; Tautz, L.; Rickert, R.C.; Mustelin, T. Protein tyrosine phosphatases in autoimmunity. Annu. Rev. Immunol., 2008, 26, 29-55.
30. Scott, L. M.; Lawrence, H. R.; Sebti, S. M.; Lawrence, N. J.; Wu, J. Targeting protein tyrosine phosphatases for anticancer drug discovery. Curr. Pharm. Des., 2010, 16, 1843-1862.
31. Heneberg, P. Use of protein tyrosine phosphatase inhibitors as promising targeted therapeutic drugs. Curr. Med. Chem., 2009, 16, 706-733.
32. Zhang, S.; Zhang, Z.-Y. PTP1B as a drug target: recent developments in PTP1B inhibitor discovery. Drug Discov. Today, 2007, 12, 373-381.
33. Nichols, A. J.; Mashal, R. D.; Balkan, B. Toward the discovery of small molecule PTP1B inhibitors for the treatment of metabolic diseases. Drug Dev. Res., 2006, 67, 559-566.
34. Heyliger, C. E.; Tahiliani, A. G.; McNeill, J. H. Effect of vanadate on elevated blood glucose and depressed cardiac performance of diabetic rats. Science, 1985, 227, 1474-1477.
35. Thompson, K. H.; Lichterb, J.; LeBelb, C.; Scaifeb, Michael. C.; McNeillc, J. H.; Orvig, C. Vanadium treatment of type 2 diabetes: A view to the future. J. Inorg. Biochem., 2009, 103, 554-558.
36. Thompson, K.H.; Orvig C. Vanadium in diabetes: 100 years from Phase 0 to Phase I. J. Inorg. Biochem., 2006, 100, 1925-1935.
37. Scior, T.; Guevara-García, A.; Bernard, P.; Do, Q.-T.; Domeyer, D.; Laufer, S. Are vanadium compounds drugable? structures and effects of antidiabetic vanadium compounds: a critical review. Mini-Rev. Med. Chem., 2005, 5, 995-1008.
38. Lyonnet, B.; Martz, E.; Martin, E. Lèmploi thérapeutique des derives du vanadium. Presse Med., 1899, 1,191-192.
39. Leighton, B.; Cooper, G. J. S.; Dacosta, C.; Foot, E. A. Peroxovanadates have full insulin-like effects on glycogen synthesis in normal and insulin-resistant skeletal muscle. Biochem. J., 1991, 276, 289-292.
40. Bevan, A. P.; Drake, P. G.; Yale, J.-F.; Shaver, A.; Posner, B. I. Peroxovanadium compounds: Biological actions and mechanism of insulin-mimesis. Mol. Cell. Biochem., 1995, 153, 49-58.
41. Fantus I. G.; Kadota, S.; Deragon, G.; Foster, B.; Posner, B. I. Pervanadate [Peroxide(s) of Vanadate] mimics insulin action in rat adipocytes via activation of the insulin receptor tyrosine kinase. Biochemistry, 1989, 28, 8864-8871.
42. Zick, Y.; Sagi-Eisenberg, R. A combination of H2O2 and vanadate concomitantly stimulates protein tyrosine phosphorylation and polyphosphoinositide breakdown in different cell lines. Biochemistry, 1990, 29, 10240-10245.
43. Garrod, D. R.; Fisher, C.; Smith, A.; Nie, Z. Pervanadate stabilizes desmosomes. Cell Adh Migr., 2008, 2, 161-166
44. Heneberg, P.; Dráberová, L.; Bambousková, M.; Pompach, P.; Dráber, P. Down-regulation of protein-tyrosine phosphatases activates an immune receptor in the absence of its translocation into lipid rafts. J. Biol. Chem., 2010, 285, 12787-12802.
45. Wang, X.; Huynh, H.; Gjörloff-Wingren, A.; Monosov, E.; Stridsberg, M.; Fukuda, M.; Mustelin, T. Enlargement of secretory vesicles by protein tyrosine phosphatase PTP-MEG2 in rat basophilic leukemia mast cells and Jurkat T cells. J. Immunol., 2002,168, 4612-4619.
46. Secrist, J. P.; Burns, L. A.; Karnitz, L.; Koretzky, G. A.; Abraham, R. T. Stimulatory effects of the protein tyrosine phosphatase inhibitor, pervanadate, on T-cell activation events. J. Biol. Chem., 1993, 268, 5886-5893.
47. Posner, B. I.; Faure, R.; Burgess, J. W.; Bevan, A. P.; Lachance, D.; Zhang-Sun, G.; Fantus, I. G.; Ng, J. B.; Hall, D. A.; Lum, B. S.; Shaver, A. Peroxovanadium compounds a new class of potent phosphotyrosine phosphatase inhibitors which are insulin mimetics. J. Biol. Chem., 1994, 269, 4596-4604.
48. Nxumalo, F.; Glover, N. R.; Tracey, A. S. Kinetics and molecular modelling studies of the inhibition of protein tyrosine phosphatases by N,N-dimethylhydroxylamine complexes of vanadium(V). J. Biol. Inorg. Chem., 1998, 3, 534-542.
49. Peters, K. G.; Davis, M. G.; Howard, B. W; Pokross, M.; Rastogi, V.; Diven, C.; Greis, K. D.; Eby-Wilkens, E.; Maier, M.; Evdokimov, A.; Soper, S.; Genbauffe, F. Mechanism of insulin sensitization by BMOV (bis maltolato oxo vanadium); unliganded vanadium (VO4) as the active component. J. Inorg. Biochem., 2003, 96, 321-330.
50. Li, M.; Ding, W.; Baruah, B.; Crans, D. C.; Wang, R. Inhibition of protein tyrosine phosphatase 1B and alkaline phosphatase by bis(maltolato)oxovanadium (IV). J. Inorg. Biochem., 2008, 102, 1846-1853.
51. Yuan, C.; Lu L.; Gao, X.; Wu, Y.; Guo, M.; Li, Y.; Fu, X.; Zhu, M. Ternary oxovanadium(IV) complexes of ONO-donor Schiff base and polypyridyl derivatives as protein tyrosine phosphatase inhibitors: synthesis, characterization, and biological activities J. Biol. Inorg. Chem., 2009, 14, 841-851.
52. Yuan, C.; Lu L.; Wu, Y.; Liu, Z.; Guo, M.; Xing, S.; Fu, X.; Zhu, M. Synthesis, characterization, and protein tyrosine phosphatases inhibition activities of oxovanadium(IV) complexes with Schiff base and polypyridyl derivatives. J. Inorg. Biochem., 2010, 104, 978-986.
53. Lu, L.; Wang, S.; Zhu, M.; Liu, Z.; Guo, M.; Xing, S.; Fu, X. Inhibition protein tyrosine phosphatases by an oxovanadium glutamate complex, Na2 [VO (Glu)2(CH3OH)] (Glu= glutamate). Biometals, 2010, 23, 1139-1147.
54. Gao, X.; Lu, L.; Zhu, M.; Yuan, C.; Ma, J.; Fu, X. Inhibitory Activities of Some Oxovanadium Complexes with N-Heterocyclic Ligands against PTP1B/ALP. Acta Chim. Sin., 2009, 67, 929-936.
55. Huyer, G.; Liu, S.; Kellyi, J.; Moffat, J.; Payette, P.; Kennedy, B.; Tsaprailis, G.; Gresser, M.J.; Ramachandran, C. Mechanism of inhibition of protein-tyrosine phosphatases by vanadate and pervanadate. J. Biol. Chem., 1997, 272, 843-851.
56. Denu, J. M.; Lohse, D. L.; Vijayalakshmi, J.; Saper, M. A.; Dixon, J. E. Visualization of intermediate and transition-state structures in protein-tyrosine phosphatase catalysis. Proc. Natl. Acad. Sci. USA, 1996, 93, 2493-2498.
57. 2+. J. Biol. Chem., 1981, 256, 6519-6522.
58. Horlein, D.; Gallis, B.; Brautigan, D. L.; Bornstein, P. Partial purification and characterization of phosphotyrosyl-protein phosphatase from ehrlich ascites tumor cell. Biochemistry, 1982, 21, 5577-5584.
59. Daum, G.; Zander, N. F.; Morse, B.; Hurwitz, D.; Schlessinger, J.; Fischer, E. H. Characterization of a human recombinant receptorlinked protein tyrosine phosphatase. J. Biol. Chem., 1991, 266, 12211-12215.
60. Tonks, N. K.; Diltz, C. D.; Fischer, E. H. Characterization of the major protein-tyrosine-phosphatases of human placenta. J. Biol. Chem., 1988, 263, 6731-6737.
61. Gebbink, M. F.; Verheijen, M. H.; Zondag, G. C.; van Etten, I.; Moolenaar, W. H. Purification and characterization of the cytoplasmic domain of human receptor-like protein tyrosine phosphatase RPTPμ. Biochemistry, 1993, 32, 13516-13522.
62. Wang, Y.; Pallen C. J. Expression and characterization of wild type, truncated, and mutant forms of the intracellular region of the receptor-like protein tyrosine phosphatase HPTPβ. J. Biol. Chem., 1992, 267, 16696-16702.
63. Zhao, Z.; Larocquen, R.; Ho, W.-T.; Fischer, E. H.; Shen, S.-H. Purification and characterization of PTP2C, a widely distributed protein tyrosine phosphatase containing two SH2 domains. J. Biol. Chem., 1994, 269, 8780-8785.
64. Haasea, H.; Maret, W. Fluctuations of cellular, available zinc modulate insulin signaling via inhibition of protein tyrosine phosphatases. J. Trace Elem. Med. Biol., 2005, 19, 37-42.
65. Haasea, H.; Maret, W. Intracellular zinc fluctuations modulate protein tyrosine phosphatase activity in insulin/insulin-like growth factor-1 signaling. Exp. Cell Res., 2003, 291, 289-298.
66. Samet, J. M.; Silbajoris, R.; Wu, W.; Graves, L. M. Tyrosine phosphatases as targets in metal-induced signaling in human airway epithelial cells. Am. J. Respir. Cell Mol. Biol., 1999, 21, 357-384.
67. 2+-induced signal initiation through the epidermal growth factor receptor. Toxicol. Appl. Pharmacol., 2003, 191, 86-93.
68. 2+. Toxicol. Appl. Pharmacol., 2006, 214, 16-23.
69. Price, K. A.; Caragounis, A.; Paterson, B. M.; Filiz, G.; Volitakis, I.; Masters, C. L.; Barnham, K. J.; Donnelly, P. S.; Crouch, P. J.; White, A. R. Sustained activation of glial cell epidermal growth factor receptor by bis(thiosemicarbazonato) metal complexes is associated with inhibition of protein tyrosine phosphatase activity. J. Med. Chem., 2009, 52, 6606-6620.
70. 2+ Ion. Arch. Biochem. Biophys., 2000, 382, 72-80.
71. Wang, Q.; Lu, L.; Yuan, C.; Pei, K.; Liu, Z.; Guo, M.; Zhu, M. Potent inhibition of protein tyrosine phosphatase 1B by copper complexes: implications for copper toxicity in biological systems. Chem. Commun., 2010, 46, 3547-3549.
72. Yuan, C.; Zhu, M.; Wang, Q.; Lu, L.; Xing, S.; Fu, X.; Jiang, Z.; Zhang, S. Potent and selective inhibition of T-cell protein tyrosine phosphatase (TCPTP) by a dinuclear copper(II) complex. (submitted).
73. Ma, L.; Lu, L.; Zhu, M.; Wang, Q.; Gao, F.; Yuan, C.; Xing, S.; Fu, X.; Mei, Y.; Gao, X. Dinuclear copper complexes of organic claw: potent inhibition of protein tyrosine phosphatases. (Submited).
74. Shaw, C. F. Gold-based therapeutic agents. Chem. Rev., 1999, 99, 2589-2600.
75. Jain, S.; Coulter, J. A.; Hounsell, A. R.; Butterworth, K. T.; McMahon, S. J.; Hyland, W. B.; Muir, M. F.; Dickson, G. R.; Prise, K. M.; Currell, F. J.; O'Sullivan, J. M.; Hirst, D. G. Cell-specific Radiosensitization by Gold Nanoparticles at Megavoltage Radiation Energies. Int. J. Radiat. Oncol. Biol. Phys., 2010, 79, 531-539.
76. Yan, K.; Lok, C. N.; Bierla, K.; Che, C. M. Gold(I) complex of N,N'-disubstituted cyclic thiourea with in vitro and in vivo anticancer properties-potent tight-binding inhibition of thioredoxin reductase. Chem. Commun., 2010, 46, 7691-7693.
77. Yan, J. J.; Chow, A. L.; Leung, C. H.; Sun, R. W.; Ma, D. L.; Che, C. M. Cyclometalated gold(III) complexes with N-heterocyclic carbene ligands as topoisomerase I poisons. Chem. Commun., 2010, 46, 3893-3895.
78. Wang, Q.; Janzen, N.; Ramachandran, C.; Jirik, F. Mechanism of inhibition of protein-tyrosine phosphatases by disodium aurothiomalate. Biochem. Pharm., 1997, 54, 703-711.
79. Krishnamurthy Divya.; Karver, M. R.; Fiorillo, E.; Orrú, V.; Stanford, S. M.; Bottini, N.; Barrios, A. M. Gold(I)-Mediated inhibition of protein tyrosine phosphatases: A detailed in vitro and cellular study. J. Med. Chem., 2008, 51, 4790-4795.
80. Karver, M. R.; Krishnamurthy, D.; Kulkarni, R. A.; Bottini, N.; Barrios, A. M. Identifying potent, selective protein tyrosine phosphatase inhibitors from a library of Au(I) complexes. J. Med. Chem., 2009, 52, 6912-6918.
81. Bashaa, S. K.; Govindarajua, K.; Manikandanb, R.; Ahnc, J. S.; Baec, E. Y.; Singaravelu, G. Phytochemical mediated gold nanoparticles and their PTP 1B inhibitory activity. Colloids Surf. B: Biointerfaces, 2010, 75, 405-409.
82. Vincent, J. B. Chromium: celebrating 50 years as an essential element? Dalton Trans., 2010, 39, 3787-3794.
83. Goldstein, B. J.; Zhu, L.; Hager, R.; Zilbering, A.; Sun, Y.; Vincent, J. B. Enhancement of post-receptor insulin signaling by trivalent chromium in hepatoma cells is associated with differential inhibition of specific protein-tyrosine phosphatases. J. Trace Elem. Exp. Med., 2001, 14, 393-404.
84. Pathak, M. K.; Yi, T. Sodium stibogluconate is a potent inhibitor of protein tyrosine phosphatases and augments cytokine responses in hemopoietic cell lines. J. Immunol., 2001, 167, 3391-3397.
85. Berggren, M. M.; Burns, L. A.; Abraham, R. T.; Powis, G. Inhibition of protein tyrosine phosphatase by the antitumor agent gallium nitrate. Cancer Res., 1993, 53, 1862-1866.
86. Gomez, M. A.; Alisaraie, L.; Tiemi Shio, M.; Berghuis, A. M.; Lebrun, C.; Gautier-Luneau, I.; Olivier, M. Protein tyrosine phosphatases are regulated by mononuclear iron dicitrate. J. Biol. Chem., 2010, 285, 24620-24628.